Home to everything from bars and craft breweries to comedy clubs and critically-acclaimed restaurants, the Windy City has a lot to offer after the sun sets. Here are a few of the best ways to spend an evening in Chicago.
Chicago’s insalubrious past has since become part of the Windy City’s allure; 1920s and ’30s-themed tours typically introduce you to former residents such as Al Capone and visit some historic speakeasies. Book an evening excursion to discover local history and enjoy classic cocktails in flapper fashion.
Craft Beer Crawls
The existence of dozens of breweries show that Chicago takes its beer seriously. Explore some of the city’s pioneering breweries and destination-worthy bars on a bar crawl or freewheeling beer tour, and leave the logistics (and driving) to your guide.
See a Show
The Windy City is packed with theaters and performance venues, all of which offer after-dark entertainment. If you’re visiting with kids, take in a blockbuster musical at the Loop’s historical theaters. Or, if you’re into late-night laughs, Chicago has a surfeit of comedy clubs, including the renowned Second City.
Combine sightseeing with dinner on an evening cruise of the Windy City’s waterways. Whether you sail on the Chicago River or head to the waters of Lake Michigan for glittering skyline views, you’ll enjoy gourmet eats, delectable wine pairings, and incomparable scenery.